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Cayman Islands

$89+ Cheap flights from Boston (BOS) to the Cayman Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — GCM
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Boston to Cayman Islands

Keep the following information in mind while searching for Boston to Cayman Islands flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$294
(United Airlines)

One-way from

$89
(JetBlue)

Popular in

April

Cheapest in

January

Average price

$598

Good round-trip deal

$320 or less

Good one-way deal

$103 or less
Provider with most accurate pricing for Boston Logan Intl-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-George Town Owen Roberts Intl flights.
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From Boston Logan Intl to Cayman Islands
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One-way flight from Boston Logan Intl to Cayman Islands
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Highest demand for flights based on searches. 4% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Boston Logan Intl to Cayman Islands.
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Price to beat on a one-way flight from Boston Logan Intl to Cayman Islands.
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Find flight deals from Boston to Cayman Islands

Cheapest flights from Boston to Cayman Islands
Explore the most affordable flight options available from Boston to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This United Airlines deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/127:36 pmBOS - GCM
2 stops17h 39mUnited Airlines
Tue 3/184:25 pmGCM - BOS
2 stops17h 34mUnited Airlines
Deal found 2/19$294
This American Airlines deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/197:11 amBOS - GCM
1 stop8h 23mAmerican Airlines
Wed 3/2612:45 pmGCM - BOS
2 stops8h 58mAmerican Airlines
Deal found 2/19$296
This Delta deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/205:40 amBOS - GCM
1 stop6h 58mDelta
Mon 3/241:03 pmGCM - BOS
1 stop11h 02mDelta
Deal found 2/19$330
This JetBlue deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/125:20 amBOS - GCM
1 stop6h 50mJetBlue
Wed 3/191:52 pmGCM - BOS
Nonstop4h 07mJetBlue
Deal found 2/19$331
This Air Canada deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/16:00 amBOS - GCM
1 stop6h 55mAir Canada
Mon 5/512:50 pmGCM - BOS
2 stops24h 42mAir Canada
Deal found 2/18$425
This Kiwi.com deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/411:33 amBOS - GCM
1 stop28h 37mMultiple Airlines
Sun 3/92:00 pmGCM - BOS
1 stop17h 52mMultiple Airlines
Deal found 2/18$451
This Mytrip deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/208:20 amBOS - CYB
2 stops34h 30mMultiple Airlines
Sun 3/233:55 pmCYB - BOS
2 stops31h 03mMultiple Airlines
Deal found 2/19$605

Find flights from Boston to Cayman Islands within your budget

Customize your flight search to find flights from Boston to Cayman Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 20, 2025.

Fly from

Boston

Fly to

Cayman Islands

Route

Depart

Return

Price

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 3/12

7:36 pm-12:15 pm

2 stops17h 39m

George Town Owen Roberts Intl

Tue 3/18

4:25 pm-10:59 am

2 stops17h 34m

$294

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Wed 3/19

7:11 am-2:34 pm

1 stop8h 23m

George Town Owen Roberts Intl

Wed 3/26

12:45 pm-10:43 pm

2 stops8h 58m

$296

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 3/10

9:47 am-1:16 pm

Nonstop4h 29m

George Town Owen Roberts Intl

Wed 3/19

1:52 pm-6:59 pm

Nonstop4h 07m

$316

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Thu 3/20

5:40 am-11:38 am

1 stop6h 58m

George Town Owen Roberts Intl

Tue 3/25

1:03 pm-1:05 am

1 stop11h 02m

$330

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Thu 5/1

6:00 am-11:55 am

1 stop6h 55m

George Town Owen Roberts Intl

Mon 5/5

12:50 pm-10:03 am

1 stop20h 13m

$425

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Tue 3/4

11:33 am-4:10 pm

1 stop28h 37m

George Town Owen Roberts Intl

Sun 3/9

2:00 pm-8:52 am

1 stop17h 52m

$451

BostonCayman Brac

BOS - CYB

BOSCYB

Boston Logan Intl

Thu 3/20

8:20 am-5:50 pm

2 stops34h 30m

Cayman Brac Gerrard-Smith

Sun 3/23

3:55 pm-11:58 pm

2 stops31h 03m

$605

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Mon 3/17

9:47 am-1:16 pm

Nonstop4h 29m

$89

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 2/28

5:00 am-2:20 pm

1 stop9h 20m

$94

BostonGeorge Town

BOS - GCM

BOSGCM

Boston Logan Intl

Fri 3/21

5:40 am-11:38 am

1 stop6h 58m

$104

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 15 results
1
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Best time to book a flight from Boston to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Boston with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Boston to Cayman Islands

Get recent, data-driven insights about flights from Boston to Cayman Islands including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Boston to Cayman Islands?

Currently, January is the cheapest month in which you can book a flight from Boston to Cayman Islands (average of $467). Flying from Boston to Cayman Islands in March is currently the most expensive (average of $594). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from BOS to KY?

Find hourly flight availability from Boston to Cayman Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

When flying from Boston to Cayman Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cayman Islands. Reviews last updated February 20, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and JetBlue from Boston to Cayman Islands to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Boston to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Boston to Cayman Islands?

    Boston Logan Intl (BOS), located 2.6 mi from the city center, is the airport you fly out of when you book flights from Boston to Cayman Islands.

  • What are the cheapest airlines to fly from Boston to Cayman Islands one-way?

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $89. Users have also found prices from $94 and $104 on American Airlines and Delta, respectively.

  • What are the cheapest flights from Boston to Cayman Islands?

    Looking at all options, your cheapest flight can be booked for $89. While the most popular route (Boston Logan Intl - George Town Owen Roberts Intl) can be booked for $277 on average our data indicates $349 when flying from Boston to Cayman Islands.

  • Can I find deals for flights from Boston to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on Boston to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Cayman Islands.

  • Can I find deals for business class flights from Boston to Cayman Islands?

    Yes. Cheapflights offers flight deals from Boston to Cayman Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Boston to Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Boston to Cayman Islands (average of $467). Flying from Boston to Cayman Islands in March is currently the most expensive (average of $594). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 6 airlines flying from Boston to Cayman Islands

Discover the top 6 airlines that operate flights from Boston to Cayman Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$234Average$559FlexibilityNo cancel feeOn-time67%
JetBlueCheapest$261Average$487FlexibilityNo cancel feeOn-time62%
DeltaCheapest$288Average$435FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$291Average$464FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$325Average$508FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$618Average$934FlexibilityNo cancel feeOn-time63%
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